Matt Dale

Matt Dale

This week, I talked to the munificent Matt Dale!

Matt is VP of Customer Support at Illuminate Education, which provides tools for K-12 educators with the mission to increase student achievement and ensure kids are graduating college-and-career ready. Matt has been with Illuminate for eight years, and has been in leadership for about nine.

Hi again, Matt! It’s not so long since we talked about our beloved vehicles over a beer in Portland, OR, right after the Support Driven Expo 2019. I’m so pleased to track you down again for this conversation about all things Customer Support!

So, can you tell me about how you got into CS?

Sure! My first job was teaching “internet skills” to at-risk students in an after-school program and then to senior citizens later in the evening through our local school district. It was in the late ’90s and Google was just starting out. Several people in the senior citizen classes wanted private lessons in their homes for more training, and so my career in support was launched. 

After I graduated college, I got a job at an Apple Authorized Service Provider in a small town in Southern California. I did hardware and software repairs, answered questions for clients on the phone and did onsite training in their homes and businesses.

I just like solving problems, helping people and generally making the world a better place!

I just like… making the world a better place!

How did you get into leading support teams?

While I was working at the tech company, I realized I wasn’t going to have opportunities to grow in my role unless I wanted to buy a share of the business and become a partner, so I decided to go back to school to get my Masters in Business Administration. 

About a year into the program, I had an opportunity to become an operations manager at a law firm. During my tenure there I learned how to manage staff, work with attorneys, handle AP/AR, deal with payroll, and basically put into practice what I was learning in my MBA program. After a year-and-a-half the partners split the firm and I decided to head back to software and got a job at Illuminate. My role was “project manager” and included helping with support calls and tickets, handling IT and doing a myriad of other things that are required in a startup. 

Over the next few years, it became clear that we needed a team lead for the support team. I was appointed to that role because of my experience in leading teams and my facility with our product and customers.

Did you find the early stages of leadership difficult?

Initially it was a rough transition. We were a relatively flat company and people had a hard time seeing me as a leader instead of a peer. We struggled most with metrics and becoming a structured team as opposed to people just doing what they wanted to. 

We struggled most with metrics

I also personally struggled with balancing my new management responsibilities with the demands of the phone and ticket queues. I needed to learn the skill of delegation, and it took me longer than it should have to get better at it.

I think this is one small difference that CS leaders often face, compared to other leadership roles out there. Many CS leaders are promoted from frontline agents as the team grows. This means that they may not be as prepared for leadership duties as some of their peers who are hired into their roles.

What skills do you need to foster to be a great CS leader? 

A lot of people think CS leadership is easy, but it requires emotional intelligence, empathy, troubleshooting skills, and delegation.

What measures of success do you use?

A mixture of metrics (CSAT, first reply time, total resolution, call time, hold time, etc.) and how the individuals on the team are feeling. The latter is more subjective, but a really important part of support team health.  

I have a love/hate relationship with metrics. They’re an important part of the story, but can be misleading. Not all calls/tickets/chats are created equal, but metrics can’t differentiate between them.

Not all calls/tickets/chats are created equal, but metrics can’t differentiate between them.

For example, an agent might take care of a customer in a call in 45 minutes that would have taken most people an hour. That’s amazing because she was efficient and skilled in communicating the knowledge properly to the customer.

In a different case, an agent might take care of a customer in 10 minutes that would have taken most people 5 minutes. In this case, the team lead would probably want to work with the agent and help him understand how to be more efficient.

In looking at both of those cases as pure metrics without context, it would appear that the second was more efficient because his call only took 10 minutes while the other agent took 45 minutes for her call. Looking at the right metrics in the right context is super important, but they don’t tell the whole story

What’s the hardest skill you’ve had to learn?

Delegation. I like to do things “right” (my way) and have a really hard time letting go of them so others can help, because they won’t do them exactly like I would. I’ve had to learn that there’s a lot of different things that are “right” not just my way, and that we’re much more effective as a team if I don’t try to do everything myself. 

We’re much more effective as a team if I don’t try to do everything myself

I’ve also gotten better at communicating what success looks like, and giving the people I’m delegating to the framework to succeed in the project. My direct reports and I have a concept of “get it 80% done” where I give them the overall spec, they put together something that’s around 80% done, and we circle back to brainstorm and provide feedback. This takes the pressure off them to polish something to 100%, and gets things turned around much quicker with much better results.

I wish I knew earlier in my career how important delegation is to our team’s success!

Has your perception of leadership changed?

I thought it would be me telling people what to do. Turns out it works better if I’m asking good questions that challenge the folks on my team to come up with better solutions than I would have come up with on my own.

It works better if I’m asking good questions that challenge the folks on my team to come up with better solutions

What’s the best resource you can recommend?

Ask A Manager. Alison Green is an amazing writer, has awesome topics on how to be a good manager, and is one of my favorite daily reads

My perennial favourite – how do you like to sign off?


Thanks Matt! I’m going to try the ‘80% done’ concept on my next project. It’s such a simple and effective idea!

Come back next week for another interview with a great CS Leader!